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Supramolecular "baking powder": a hexameric halogen-bonded phosphonium salt cage encapsulates and functionalises small-molecule carbonyl compounds.

Joseph M MarrettHatem M TitiYong TeohTomislav Friščić
Published in: Chemical science (2023)
We report a hexameric supramolecular cage assembled from the components of a Wittig-type phosphonium salt, held together by charge-assisted halogen bonds. The cage reliably encapsulates small polar molecules, including aldehydes and ketones, to provide host-guest systems where components are pre-formulated in a near-ideal stoichiometry for a mechanochemical base-activated Wittig olefination. These pre-formulated solids represent a proof-of-principle for a previously not reported supramolecular design of solid-state reactivity in which the host for molecular inclusion also acts as a complementary reagent for the subsequent chemical transformation of an array of guests. The host-guest solid-state complexes can act as supramolecular surrogates to their Wittig olefination vinylbromide products in a Sonogashira-type coupling that enables one-pot mechanochemical conversion of an aldehyde to an enediyne.
Keyphrases
  • solid state
  • water soluble
  • small molecule
  • ionic liquid
  • energy transfer
  • high throughput
  • mass spectrometry
  • quantum dots